ArticleNature communications2021
Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Investigating Opioid Receptor Activity through Biocatalytic Halogenation and Oxidation of Mitragynine.ACS chemical biology · 2026Article
- Engineered Flavin-Dependent Halogenases Catalyze C-C Bond Formation via Enantioselective Semipinacol Rearrangement.Journal of the American Chemical Society · 2026Article
- Photoenzymatic catalysis enables enantioselective radical dearomative spirocyclization.Nature communications · 2025Article
- Genome Mining of Isoindolinone-Containing Peptide Natural Products.Journal of the American Chemical Society · 2025Article
- The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.Chemical reviews · 2025Review
- In silico ligand self-assembly drives binding recognition of natural products intoIn silico pharmacology · 2025Article
- Distinct Characteristic Binding Modes of Benzofuran Core Inhibitors to Diverse Genotypes of Hepatitis C Virus NS5B Polymerase: A Molecular Simulation Study.International journal of molecular sciences · 2024Article
- Mechanism of Nitrone Formation by a Flavin-Dependent Monooxygenase.Biochemistry · 2024Article
- Exploring the synthetic potential of epoxide ring opening reactions toward the synthesis of alkaloids and terpenoids: a review.RSC advances · 2024Review
- Biocatalytic Stereoselective Oxidation of 2-Arylindoles.Journal of the American Chemical Society · 2024Article
- Triepoxide formation by a flavin-dependent monooxygenase in monensin biosynthesis.Nature communications · 2023Article
- Fungal P450 Deconstructs the 2,5-Diazabicyclo[2.2.2]octane RingJournal of the American Chemical Society · 2023Article
- Novel Functionalized Spiro [Indoline-3,5'-pyrroline]-2,2'dione Derivatives: Synthesis, Characterization, Drug-Likeness, ADME, and Anticancer Potential.International journal of molecular sciences · 2023Article
- An NmrA-like enzyme-catalysed redox-mediated Diels-Alder cycloaddition with anti-selectivity.Nature chemistry · 2023Article
- Microwave-assisted synthesis, antioxidant activity, docking simulation, and DFT analysis of different heterocyclic compounds.Scientific reports · 2023Article
- Discovery of a cytochrome P450 enzyme catalyzing the formation of spirooxindole alkaloid scaffold.Frontiers in plant science · 2023Article
- Unraveling the biosynthesis of penicillenols by genome mining PKS-NRPS gene clusters inAIChE journal. American Institute of Chemical Engineers · 2022Article
- Electrochemical oxidative rearrangement of tetrahydro-β-carbolines in a zero-gap flow cell.Chemical science · 2022Article
- Citrinadin C, a new cytotoxic pentacyclic alkaloid from marine-derived fungus Penicillium citrinum.The Journal of antibiotics · 2022Article
- Rational design of allosteric switchable catalysts.Exploration (Beijing, China) · 2022Review
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13 authors.
Funding
Abstract
Prenylated indole alkaloids featuring spirooxindole rings possess a 3R or 3S carbon stereocenter, which determines the bioactivities of these compounds. Despite the stereoselective advantages of spirooxindole biosynthesis compared with those of organic synthesis, the biocatalytic mechanism for controlling the 3R or 3S-spirooxindole formation has been elusive. Here, we report an oxygenase/semipinacolase CtdE that specifies the 3S-spirooxindole construction in the biosynthesis of 21R-citrinadin A. High-resolution X-ray crystal structures of CtdE with the substrate and cofactor, together with site-directed mutagenesis and computational studies, illustrate the catalytic mechanisms for the possible β-face epoxidation followed by a regioselective collapse of the epoxide intermediate, which triggers semipinacol rearrangement to form the 3S-spirooxindole. Comparing CtdE with PhqK, which catalyzes the formation of the 3R-spirooxindole, we reveal an evolutionary branch of CtdE in specific 3S spirocyclization. Our study provides deeper insights into the stereoselective catalytic machinery, which is important for the biocatalysis design to synthesize spirooxindole pharmaceuticals.
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